New work holidays promise all the relaxation of a break but with the chance to grow your business too.
Photograph: Spaces/Getty/Blend

Most small business owners know the double-bind that comes with taking a holiday. You desperately need a break and know your business is suffering for it, but the worry about taking off a week – or God forbid, two weeks – is too great.

What if something goes wrong and nobody can reach you? What if you miss out on that one order or deal that is going to make your business?

Spending money that could go into the business on a holiday where all you do is worry doesn’t seem like a great investment. But now, a new generation of holiday companies aim to bridge the gap between work and play.

Remote Year, Coboat and Flock all want you to pack your laptop and flip-flops and go on holiday with them. This new breed of business bootcamps take entrepreneurs and freelancers to specific destinations. They sort out the accommodation, organise trips and events and promise all the rejuvenation of a holiday but with the added bonus of helping your business at the same time.

Flock, which expands the idea of a city break, started two years ago when a group of female entrepreneurs (and, full disclosure, myself) realised they all had work in New York but were putting off trips because of the expense, the fear that it wouldn’t be worth it, and the reluctance to fly long-haul for one or two meetings and three nights in a hotel by themselves. They formed a sort of collective, living and working in an AirBnB house for a week, introducing contacts, hosting joint events and mentoring each other. The week was such a success that two of the original members, Emma Sexton and Megan Thomas, turned it into a business. They’ve run two trips so far and have a third coming up.

For Sexton the trip worked, and created a business opportunity for two reasons: “Firstly, we were able to explore the US market which gave everyone confidence and bigger ambitions for their businesses. Secondly – the vulnerability – everyone was very open about their hopes and fears, which created a deep friendship bond that all of us still have between us today. For us all it was a great, alternative, way to do ‘business’ and we wanted to give that experience to more entrepreneurs.”

Remote Year, a travel company touring 12 countries in 12 months, started in a similar way. Founder Greg Caplan had been planning to travel and work remotely after finishing a year at Groupon. Lining up remote work, he asked friends if they wanted to travel with him while also working. None of them could, so he turned to the internet to find a group of friends to travel with – and that was the first Remote Year programme.

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But can you really mix travel with running a successful business or is it the worst of both worlds? We take a break to relax and recharge; can you do that if you’re taking your work with you?

Emma Mclaren, a consultant for the Sustainable Fisheries Partnership, is currently on board Coboat. A co-working space and holiday, Coboat allows entrepreneurs to sail the seven seas while working. For Mclaren the idea that travel would interfere with work, or vice versa, has never been a problem.

“I think our ability to switch off is a challenge regardless of whether you take ‘pure’ holidays or combine travel and work: technology has changed this for many workers. When you’re travelling and exploring, work can become a lot more efficient. I find I have more self-motivation to get the work done so I can take advantage of my surroundings – be that scuba-diving, walking around a new city or reading in a local café.”

The idea of using these holidays to focus your working practices is one that is echoed by people who’ve been on them – but can you really grow your business while you’re exploring new places? Doesn’t the lure of an afternoon walking around somewhere beautiful make putting off responding to those emails a bit too easy?

Rebecca Rubin, CEO of marketing and mindset mentoring company, the Pursuit of Fabulous, disagrees. She’s spending 12 months travelling as part of Remote Year and feels it’s only been good for her business.

“I assumed that travelling would distract me from my business but there have been unexpected plus sides. Two people in my group have become clients, I’ve hired two others,” says Rubin. “I also think that living my life in a way that is unconventional and adventurous – traveling to 12 countries in 12 months while running my business from my laptop – is inspiring to potential clients: they want to create something similar for themselves.”

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If you’re planning on travelling for a while, there are things to think about first. Rubin praises Remote Year for ensuring that you don’t have to worry about things like Wi-Fi access, or where to hold a meeting, or whether you’ll get lonely. Both Flock and Coboat see themselves as bringing together like-minded people who will bounce off and help each other. It’s your job to turn up and add to the atmosphere, they’ll take care of everything else. The network you build through these trips is also invaluable.

“I’ve learned your network is everything,” said Sophia Story, head of commercial at 3 Sided Cube, an app development company, who went on the last Flock trip. “The magic happened in the unplanned sessions; being in the same house forced unplanned conversations. Barriers were down and people spoke honestly. This is what was valuable ... people being open with opinions and experience. Meeting just one or two key individuals can open up networks you didn’t even know existed.”

All holiday companies stress the importance of being someone who wants an adventure, is happy to collaborate and will share knowledge with others. It’s not for everyone and if you truly want to switch off and pretend that work doesn’t exist for a while, then it’s definitely not for you. Like most entrepreneurs, the people on these trips are passionate about what they do and the idea of forgetting about it for two weeks doesn’t really appeal.

As Flock alumni Natalie Campbell, a founder and director at social innovation consultancy, A Very Good Company, puts it: “I love my work so I don’t holiday to escape or run from it, I holiday for perspective and downtime from being on the go in meetings.” She adds that most entrepreneurs feel guilty about taking a holiday anyway, so working holidays are a way to avoid that. “It’s the perfect blend of time away while still moving my business forward.”

Find the right working holiday and it could be good for you and your business. Now you just have to find your passport.

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